Diisopropylethylamine → 6-Benzyl-3-methyl-1,6-diazaspiro[3.4]octan-5-one

HRID 1912432Notes

Reaction equation

HRID 1912432 reaction equation
C(O[C:6](=O)[CH2:7][N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:9]([CH3:12])CO)(C)(C)C.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[N:37]1(OC(N(C)C)=[N+](C)C)[C:41]2N=CC=[CH:45][C:40]=2N=N1.C(=O)(O)[O-:55].[Na+]>C(Cl)(Cl)Cl.O>[CH2:13]([N:8]1[CH2:7][CH2:6][C:12]2([NH:37][CH2:41][CH:40]2[CH3:45])[C:9]1=[O:55])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58293285[Benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid tert-butyl ester

Product 1

HCID 582933106-Benzyl-3-methyl-1,6-diazaspiro[3.4]octan-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of an optically-active compound of 2-(2-benzylaminoethyl)-3-methylazetidine-2-dicarboxylic acid 2 hydrochloride (29.1 g) and N,N-diisopropylethylamine (65 ml) in chloroform (290 ml) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (41.3 g) at room temperature, and the mixture was stirred for 4 hours. To the reaction mixture were added saturated aqueous sodium bicarbonate solution (200 ml) and water (100 ml), and the mixture was extracted with chloroform (200 ml). The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 10/1) to give the titled compound (21.3 g).

Workup

  1. extractionthe mixture was extracted with chloroform (200 ml)
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-ddf6417373e94bbea796931eafa0421d
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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